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Development of a generic activation mode: nucleophilic α-substitution of ketones via oxy-allyl cations

Author(s): Vander Wal, Mark N.; Dilger, Andrew K.; MacMillan, David W.C.

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dc.contributor.authorVander Wal, Mark N.-
dc.contributor.authorDilger, Andrew K.-
dc.contributor.authorMacMillan, David W.C.-
dc.date.accessioned2020-10-30T19:08:12Z-
dc.date.available2020-10-30T19:08:12Z-
dc.date.issued2013-6-11en_US
dc.identifier.citationVander Wal, Mark N., Dilger, Andrew K., MacMillan, David W.C. (2013). Development of a generic activation mode: nucleophilic α-substitution of ketones via oxy-allyl cations. Chemical Science, 4 (8), 3075 - 3075. doi:10.1039/c3sc51266een_US
dc.identifier.issn2041-6520-
dc.identifier.urihttp://arks.princeton.edu/ark:/88435/pr1xj8d-
dc.description.abstractOxy-allyl cations have been known as transient electrophilic species since they were first proposed as intermediates in the Favorskii rearrangement in 1894. Since that time, they also have been used as a mode of activation for [4 + 3] cycloadditions in a variety of natural product syntheses. In this manuscript, we describe a method for the interception of oxy-allyl cations with a diverse range of common nucleophiles, thereby demonstrating the value of this intermediate as a generic mode of activation. This simple, mild, room temperature protocol allows for the formation of a variety of high value carbon–carbon and carbon–heteroatom bonds that are readily incorporated within a series of cyclic and acyclic ketone systems. Initial efforts into the development of an enantioselective catalytic variant are also described.en_US
dc.format.extent4, 3075 - 3075en_US
dc.language.isoenen_US
dc.relation.ispartofChemical Scienceen_US
dc.rightsFinal published version. This is an open access article.en_US
dc.titleDevelopment of a generic activation mode: nucleophilic α-substitution of ketones via oxy-allyl cationsen_US
dc.typeJournal Articleen_US
dc.identifier.doidoi:10.1039/c3sc51266e-
dc.identifier.eissn2041-6539-
pu.type.symplectichttp://www.symplectic.co.uk/publications/atom-terms/1.0/journal-articleen_US

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